


Riding Larry

by TobytheWise



Category: Supernatural
Genre: 69 (Sex Position), Alternate Universe - Modern Setting, Anal Fingering, Anal Sex, Bottom Dean, Castiel/Dean Winchester First Kiss, Coming Untouched, Dean Winchester Has a Cowboy Kink, Halloween Costumes, Love Confessions, M/M, Oral Sex, Plot What Plot/Porn Without Plot, Porn with Feelings, Rimming, Size Kink, Size Queen Dean, Top Castiel
Language: English
Status: Completed
Published: 2017-12-26
Updated: 2017-12-26
Packaged: 2019-02-20 16:48:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,322
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13150845
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: Dean has been in love with his best friend, Castiel, since they met in college. Dean gets to their annual halloween costume party to discover that Cas has a dirty plan to seduce Dean. And unsurprisingly, Dean is completely on board with this plan.





	Riding Larry

**Author's Note:**

> This story goes out to my secret santa as their Christmas gift! Everyone else, I hope you enjoy as well!! (PS if you give the gift of steamy porn for Christmas does that put you on Santa's naughty or nice list??)

Dean makes his way into his best friend’s house. Every year since they graduated college, Cas has thrown a blowout Halloween party. Every year, it’s crazy and wild and insanely fun. This year, the two agreed to do a set costume. Dean straightens his vest and makes sure his gun holster is on straight. His costume looks perfect in his opinion and he’s excited to see Cas in his.

The door opens and Dean’s assaulted with loud music, body heat, and the smell of beer. Sometimes he thinks they’re too damn old for college style parties. But then again, he probably thinks that because he’s still sober. Time to change that.

Dean walks to where he knows is the kitchen. A small bundle of red head jumps into his arms with an excited giggle.

“Dean!” Charlie screams and Dean knows she must have been here for awhile. He twirls her around and sets her down on the ground. Charlie grabs his arms and pulls him deeper into the kitchen as she sings about having more shots.

Dean takes the two shot glasses she forces into his hands and swallows them down one right after the other. It’s some fruity shot that he’ll never admit to really liking. He licks the remnants off his lips and looks back at his friend.

“Dude! I’m so glad you made it! And I love the costume! You’re pulling off the Han Solo look.” He feels his neck flush with embarrassment. Dean’s never been good at taking a compliment but in all honestly he does feel good in this outfit. He’s feeling hotter and more confident than usual.

“Thanks, Charlie. And you’re looking awesome in your costume.”

Charlie is dressed as Hermione and she swings her wand right in his face. Dean has to dodge so the damn thing doesn’t poke him in the eye.

“I know I am. No one beats Hermione.” Her face lights up as she sees someone walk past the door. When Dean turns around the person’s already gone. “You are going to go crazy over Cas’s costume. You’re just gonna love it,” Charlie starts giggling again. “Oh my gosh, I can’t wait to see your face.”

Dean doesn’t hide his confusion. Cas is supposed to be dressed as Luke Skywalker. They had this planned for months now. “What are you giggling about, Charlie?”

She snorts and pulls something out of her pocket and slaps it into his hand. He looks down to find a Magnum XL condom in his palm and his face heats up. “You’re gonna need this,” she says as she laughs and walks away. Dean quickly hides the condom in his pocket before someone can see him standing here holding it.

Dean grabs himself another shot before finding himself a beer. He’s not dealing with his obnoxious friends without a buzz.

Then Dean goes out into the living area to try and find his best friend. He’s looking through the crowd for a white robe and can’t find Cas anywhere. When he finally spots Cas, Dean is first confused and then uncontrollably aroused. His mouth goes dry and his heartbeat speeds up. Dean can feel his face flush and his cock harden.

Standing in the corner of the room is his best friend dressed not as Luke Skywalker but a cowboy.

“Fuck,” Dean breathes to himself. All of his friends know and tease him about his arousal towards everything cowboy. Sam even goes so far as to calling it his fetish but he’s never had to deal with it in the real world before. Seeing Cas like this is driving Dean crazy with lust.

Cas is dressed in tight dark jeans, that hug his ass perfectly, underneath dark assless chaps. His shirt is tucked into his jeans and unbuttoned to the very last two buttons leaving Cas’s tanned and sculpted chest exposed. He’s got a black sheriffs vest on his shoulders. The look is complete with cowboy boots and a cowboy hat. Dean tries to adjust his pants as subtly as possible and hopes they’re not too tented in the front for everyone to see.

Dean debates whether or not he should just turn around and walk out when he’s met with a stare by his favorite pair of blue eyes. The look Cas gives him makes him shudder with excitement and he tries to put a stop to it. They’re best friends. Yes, Dean’s loved his best friend since they met but that doesn’t mean Cas feels the same way. There’s no way Dean’s going to make him uncomfortable by making his incredibly overactive libido get in the way.

Cas nods his head, gesturing Dean forward. Dean takes a deep breath and puts one foot in front of the other. He can do this. Cas begins to stride towards him. They meet in the middle of the living area which is being used as a dance floor.

Cas says something that Dean can’t hear due to the loud music. He shakes his head to let Cas know he can’t hear. Cas just smiles and pulls Dean forward until they’re chest to chest and Cas can lean in and talk right into Dean’s ear. Dean feels his body respond immediately to the closeness. He’s so close he can smell Cas’s cologne and he wills his cock to deflate but instead it only gets harder.

“Hello, Dean. I’m glad to finally see you.” Dean feels himself shudder again. The feel of Castiel’s breath right against his ear is driving him mad.

“Heya Cas. Nice party you got going on. What’s up with the costume? I thought you were going to be Luke to my Han.”

Cas just shrugs in a way that Dean feels more than sees. “I thought you’d like this one better.”

When they pull apart, Dean notices they’ve begun to sway together with the beat of the song that’s playing. Dean sees something playful dancing in those beautiful blue eyes right before Cas swings his arms forward around Dean’s neck and then they’re dancing.

Dean feels hypnotized. He can’t stop swaying to the music with his eyes glued to his best friend. Cas is sexy in the way he rolls his hips and moves his body all while keeping eye contact with Dean.

Cas smiles a dirty smile and grabs Dean by the hips. Dean’s feels his heart leap into his throat as Cas turns him around and pulls his hips back to meet his own. Dean lets out a moan of surprise to being back to chest with Cas. He can feel the long, lean line of Castiel’s chest and it’s driving him mad.

“Show me how you can move, Dean,” Cas growls right into his ear. Dean can feel a zing race up his spine. He’s wanted Cas for so long and he doesn’t want to hold his self back anymore.

Dean grinds back into Cas’s lap and he feels Cas hum in approval. He moves his hips back and forth to the music and he can feel in the way that Cas’s grip on his hips tighten, that Cas is loving this just as much as he is. Dean reaches his arm above his head and pulls it down until its against the back of Cas’s neck. He pulls on the hair behind Cas’s head and Cas moves his head forward until his mouth is right as Dean’s neck.

Dean can feel goosebumps explode across his body when he feels the slightest touch of Cas’s lips to his neck.

“Oh god, Cas,” Dean groans. He feels entirely wanton and he can’t find it in himself to stop. He feels confident and sexy and he wants Cas to know it too.

“Fuck, Dean. Do you know how sexy you are?”

Dean presses his ass harder against Cas’s crotch and is reward with the feel of the hard line of his erection. He feels Cas begin to nip and suck at the point where his neck meets his shoulder and it makes his own cock feel diamond hard. He wants Cas so bad.

“Cas, fuck, don’t do that if you don’t mean it.”

Cas bites down hard on Dean’s neck and Dean can’t stop the long, low moan that escapes his lips. Cas quickly soothes the bite with a light kiss before saying, “I want you so bad, Dean. I’ve wanted you for so long.”

Dean feels like a dam bursts in his chest. There’s no more subtle, there’s no more holding back. He can have this. Dean takes exactly what he wants. He twirls around in Cas’s arms and wraps his arms around his neck. He pulls them together until their chest to chest and plants his lips firmly on Cas’s.

They both moan into the kiss. Dean feels like his body is completely lite up with fireworks. No other kiss has felt like this. Cas pulls back to look Dean in the eyes and Dean groans seeing Cas’s face spelling out his lust.

“My room. Now.”

Dean grabs his hand and drags him up the stairs towards Cas’s bedroom. When they get inside and lock the door, Cas is on him in a heartbeat. Cas’s hands run all over his chest and in his hair as he devours Dean’s mouth with his tongue. It feels amazing. The only thing more amazing is if they had on less clothes.

Dean gets to work and getting Cas’s out of the way. He takes off Cas’s hat and tosses it towards the bed. Then he takes off his sheriff’s vest and white button up shirt.

“You’re such a sexy sheriff. Did you wear this costume knowing what it would do to me?”

Cas chuckles and nods his head. “Yeah,” he says between laying kisses on Dean’s neck, “I knew it would drive you crazy. Give me the opportunity to seduce you.”

“Fuck. It worked,” Dean punctuates this by grinding his erection into Cas’s thigh. Cas groans in answer before starting to pull of Dean’s shirt.

Once they’re both left with bare chests, Dean falls to his knees and begin working on getting Cas out of his pants. First, Dean reaches down and takes the cowboy boots off. Then he works on getting the chaps off. His face is so close to Cas’s dick his mouth waters in anticipation.

Dean wants nothing more than to have that dick in his mouth and sooner the better. He just hopes that it’s as big as he’s heard. Dean’s hands shake as they begin unbuttoning Cas’s jeans. He pulls down the zipper and then tugs the jeans down to Cas’s ankles.

Dean groans when he sees the outline of Cas’s erection. He hasn’t even laid eyes on it yet but he already knows he’s going to love this cock.

Cas pulls him up from his knees and they kiss briefly before Cas is the one falling to his knees. He gets Dean out of his Han Solo boots and pants and surprises Dean by pulling his underwear off right away too. Cas stands up and leaves his boxers on the ground too.

“Oh fuck,” Dean says as his eyes immediately attach to Cas’s cock. Dean reaches a hand forward and grabs onto Castiel’s cock. It’s the biggest cock he’s ever seen and he can’t wait to feel it. “Oh god, Cas. You’re fucking cock.”

“I know it’s intimidating.” Dean stops his hand and looks up at Cas in surprise.

“What?”

“I realize you won’t want to bottom and that’s okay. No one’s ever wanted to bottom. I don’t mind having to bottom so it’s not a big deal, Dean,” Cas rambles.

“Fuck no!” Dean interrupts before Cas can continue. “I am getting this thing inside me tonight,” punctuating his sentence by squeezing Cas’s cock. “I want this beautiful, perfect cock inside me so fucking bad, Cas. This is the most perfect dick I’ve ever seen. Please let me have it inside me.”

Cas surges forward and kisses Dean hard. He pushes Dean forward until he falls down onto the bed on his back. Cas goes through his drawer and grabs a bottle of lube before laying on the bed beside Dean. Cas lays on his back and pulls Dean onto his lap backwards. Then he pulls Dean back so Dean’s face is right in front of Castiel’s beautiful monster of a cock.

Dean’s mouth waters and he can’t stop himself from leaning forward and licking at the slit. The bitter and salty taste of Cas’s precome fills his mouth and makes him hungry for so much more.

Dean is completely caught off guard when he feels Cas pull his ass cheeks apart and immediately begin licking his taint and asshole.

“Shit, Cas! No one’s ever done that to me before!”

Cas pulls back and meets Dean’s eyes. “Do you want me to stop?”

“Fuck no! Eat my ass.” Cas digs back in with enthusiasm. It’s like nothing Dean has ever felt before. To keep himself from focusing too hard and coming too early, Dean pulls Cas’s cock to standing and wraps his lips around the head. He swirls his tongue around and he can feel Cas groan. The vibrations rumble in his hole and it makes his thighs tremble in pleasure.

He feels Cas continue to lick and suck on his hole as he begins to open Dean up with lubed up fingers. It feels so good and he can’t wait to feel all of Cas inside him.

Dean wishes he had a bigger mouth or a better gag reflex so he could fit more of Castiel’s dick into his mouth but he settles for jerking his hand around the bottom that doesn’t fit. Occasionally he moves down and plays with Cas’s ball with his tongue before going back to his cock.

Dean can feel himself getting closer and closer to the edge but he’s determined not to come until he has Cas’s cock in his ass. Once, Cas is about three fingers deep he’s not sure he can wait too much longer.

“Cas, ease up with your tongue.”

Cas pulls his mouth back but continues with his fingers. “You still okay?”

Dean nods his head, “Yeah, I’m really fucking good. I just don’t want to come yet.” Then he wiggles his ass a little bit, “Are you almost done?”

Cas nips at his left cheek before smoothing it over with his lips. “Almost. I want one more finger stretching you out first. I don’t want to hurt you, baby.”

The endearment makes Dean’s chest light up with pleasure. It feels so right for Cas to call him that and it makes him feel loved and wanted. Dean can feel the stretch of another finger and he knows that Cas has added the fourth one. He just needs to be a little more patient and he’ll have exactly what he wants.

“Cas, I can’t wait much longer,” Dean whines.

“Okay, turn around.” Cas pulls his fingers out as gingerly as possible and swats Dean on the ass. Dean feels so incredibly empty and he freaking hates it. He needs this giant dick in his ass yesterday and now he’s got no reason to wait.

He gets off of Cas’s and turns around so they’re facing each other again. Dean sees Cas rummaging around in his nightstand before flopping back down onto the bed with a look of defeat on his face.

“I don’t have any condoms,” Cas says while looking like he’s in actual pain just saying that. And Dean understands.

Dean gets out of bed as quickly as he can and finds his Han Solo costume. Inside the pocket is that damn Magnum XL condom that Charlie gave him. He pulls it out and flashes it at Cas with a smile. On his way back into the bed, Dean reaches down and places the cowboy hat on his head.

Dean opens the condom and slides it down onto Cas’s erection before saying, “Get ready, babe. Every Friday night I go and ride Larry and that mechanical bull’s seen nothing compared to what I’m about to do to you.”

Instead of being seductive like Dean expected, Cas bursts out laughing. He reaches forward and tosses the cowboy hat off of Dean onto the floor. Cas leans forward until they’re chest to chest again and pulls Dean down into a kiss. While kissing, Cas pours lube onto his erection so it’s completely slicked for Dean.

Dean lifts himself up while Cas lines up his cock. He slowly sits himself down and his breath hitches at the feel. Of course there’s a burn even with all the prep Cas did but under that is complete and utter bliss. Dean feels so full and so good that he can barely breathe.

Dean leans his forehead onto Cas’s and they stare at each other until Dean is completely seated in Cas’s lap.

“Dean, you feel so good. So fucking tight.”

Dean clenches his muscles to squeeze Cas’s cock even tighter, making the other man groan. “You’re cock is filling me up so perfectly, Cas. Never had a cock this big before.”

Cas places his hands on Dean’s neck and the gentle gesture stirs butterflies in Dean’s stomach. “I was worried,” Cas says while biting his lips. “I’ve heard rumors that you broke up with Aaron and Benny because you were a size queen.”

Dean can’t stop himself from laughing. “There were more reasons than that why I broke up with them.” Dean makes himself concentrate. Which is difficult with this perfect cock in his ass but what he has to say is important. “I was in love with someone else when I was dating them. It would have never worked out.”

Cas seems to think about this for a moment before asking, “And now, with us?”

Dean smiles, “The person I’m in love with is literally inside me right now. And you have nothing to worry about, baby. I used to fuck myself on my biggest dildo imagining it was you and Cas, you’re even bigger than that.”

Cas begins to slowly rock his hips up into Dean and Dean closes his eyes in pleasure. He rolls his hips with Cas and they begin a steady rhythm. Dean tilts his hips until Cas is drilling into Dean’s prostate with every thrust.

“Fuck, Cas. I’m so close.” Pleasure surges through Dean with every movement and he feels like his skin is on fire. Everything feels so heightened and surreal. He can’t wrap his mind around the fact that he just told his best friend he loved him. This is real and it feels amazing.

“Dean, look at me.” Dean snaps his eyes open and finds Cas’s blue eyes. “I love you too.” And just like that Dean is coming across both of their chests completely untouched. His orgasm feels like it goes on and on and on. He’s not sure how long he squirts long ropes of cum until he falls forward into Cas’s arms.

Cas fucks Dean through and after a few more thrusts is stilling and coming inside Dean. Cas gently pulls Dean onto his side and pulls out of him. They lie on their sides looking at each other. Cas runs his fingers through Dean’s hair and Dean rubs his hand up and down Cas’s hip.

Dean’s not sure how long they sit there, staring at each other and breathing each. It’s peaceful and perfect.

“I love you,” Dean crocks out.

“I love you too. So much.”                                  

“Why in the hell did we wait so long to do that? That was amazing,” Dean says dreamily. He’s already trying to figure out how long it will take for Cas to get hard again so they can have round two.

“Better than Larry?” Cas asks with a smirk.

Dean rolls on top of Cas and kisses him silly before answering. “Hell yeah, better than Larry.”


End file.
